Anthracene dye and process of making same.



MAX HENRY ISLER, OF MANNHEIM, GERMANY, ASSIGNOR TO BADISCHE ANILIN & SODA FABRIK, MANY, A CORPORATION.

OF LUDW'IGSHAFEN-ON-THE-HHINE, GER- ANTHRAOENE DYE AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

Patented Dec 4, 1906.

Application filed September 20, 1905. Serial No. 279,366.

To all whom, it 'l I'l/H/Z/ amt/2min:

' Be it known that I, i\'l.AX HExRY IsLER,

and printing, and especially dyeing and printing vegetablefiber.

The derivatives of beta-methyhanthraquiiron which can be employed for the purposes of my invention include those in which a hy. drogen atom or hydrogen atoms of the methyl group is or are replaced by a halogen atom or atoms.

The condensing agents which I have found to be suitable for the purposes of my invention include the caustic alkalies, preferably in alcoholic solution and with or without the addition of an acetate. The new compound can be recrystallized from nitrobenzene, and thus be obtained in the form of golden-yellow crystals which are difficultly soluble in benzene, alcohol, 6th6l',&fld acetone, but are soluble in concentrated sulfuric acid, the solu-v tion being bluish red: They are insoluble in caustic-alkali solution, but on treatment with alkaline reducing agents they are converted into the hydro compound, which is soluble in the alkaline solution with a brown-red color. The vat thus obtained dyes cotton brown-red shades, which upon washing, or more quickly upon treatment with dilute sodium hypochlorite solution, are converted into pure-yellow shades'of excellent fastness against the action of washing, chlorin, light, and boiling with dilute acids.

For use in printing the new compound can .be printed, together with caustic alkali and with or without a reducing agent onto the material, which is afterward steamed, or a mixture of the coloring-matter with a reducing agent can be applied to the material, which is afterward passed through an alkaline bath.

The following examples illustrate how my invention can be carried into practical effect; but it is not limited to these examples. The parts are by weight.

' to sixty minutes,

Example 1. I

Heat together for from one (1) to two (2) hours at a temperature of from one hundred and fifty (150) to one hundred and seventy (170) degrees centigrade one (1) part of betamethyl-anthraquinon, four (4) parts of potassium hydrate, and four (4) partsof alcohol. Pour the melt into water and boil for some time or else add some sodium hypochlorite to the solution in order to oxidize any hydro compound which may be present and then filter. If desired, an oxidizing agent-for instance, potassium. nitrate or potassium chloratemay be added to the .melt at the start,

in which case the temperature need not be raised above from one hundred and forty to one hundred and fifty degrees centigrade. The product obtained canbe recrystallized from nitrob'enzene and be thus obtained in the form of golden-yellow crystals, which are diilicultly soluble in alcohol, ether, benzene, and acetone, but which dissolve in concentrated sulfuric acid,yielding a beautiful bluish-red solution. They are insoluble in caustic-alkali solution, but are soluble in alkaline solutions of reducing agents, being reduced to the hydro compound and yielding a brownish-red vat.

Example 2. Heat together for about. one (1) hour at a temperature of from one hundred and. sixty to one hundred and seventy degrees ce'ntigrade one (1) part of omega-dichlorbeta methyl anthraquinon, (C H (CO) C H .CHGl,,) hydrate, and four (4) parts of alcohol. Pour the melt into water, boil for from-thirty (30) and filter off the reaction product. In this example the mono chlor compound can be used instead of or in admixture with the omega-dichlor-betamethylanthraquinon or bromin derivatives can be employed. It is not necessary to work always with alcoholic potash, as the reaction also proceeds well if, for instance, one (1) part of omega-monochlorbeta-methylanthraquinon, four (4) parts of potas ium hydrate, and one drous sodium acetate be, heated together for about one (1) hour ata temperature of from one hundred and seventy (170) to one hundred and eighty degrees centigrade.

the corresponding four (4) parts of potassium (1) part of anhynot can be obtained in the .or with nitrobenzene or while heating. Instead of lead oxid otheroX1dssuch, for instance,

, v Example 8.

Heat together two (2) parts of beta-methylanthraquinon and oxid for a few hours at a temperature of from three hundred and twenty (320) to three hun- (340) degrees centigrade until sistency, becomes hard. The reaction prodpure form by extracting with alkaline hydrosulfite solution anilin or pyridin as copper oxid or barium oxidcan be employed.

' Example 4.

Heat together toclaveat, atemperature of from two hunfdred and ten (210) to two hundred and twenty (220) degrees centigrade one 1) part of omega-dichlor-beta-methyl-anthraquinon and twenty (20) parts of twenty (20) per zenei dition of the it assists in cent. milk of lime. After cooling dissolve away the lime by means of hydrochloric acid residue from nit-robenand recrystallize the In all cases the same product is finally obtained.

Example 5. Conversion of the New Coloring- Matter into its Hydro Compound for Use in y gl I Stir well together one thousand (1,000) parts of water at a temperature of from fifty (50) to sixty (60) degrees centigrade, one-half (.5) part of the new coloring-matter which has previously been made into a paste with about twenty-five (25) parts of water, twentyfive (25) arts of caustic-soda solution (containing about twenty-four (24) per cent. of NaOH) and from ten (10) to fifteen parts of a twenty per cent. hydrosulfites0lution. Work fifty (50) parts of cotton in this bath for from thirty O) to forty-five (45) minutes, wash well, an work up. The bath does not become completely exhausted; but bythe addition of from twenty-five to fifty (50) parts of common salt or of Glau, ber salt the coloring-matter is used up to a greater degree. I

Example 6. Use of the New O0Z0ring-ll1atter for Printing.

A. Process with subsequent use of causticallcalibath-Prepare a paste containing two hundred (200) parts of a ten (10) per cent.

:paste of the new coloring-matter, one hundred and twenty (120) parts of iron vitriol, twenty (20) parts of tin chlorid, two hundred and sixty (460) parts of thickening. The adtartaric acid is not essential; but the subsequent removal of the three (3) parts of lead cent. of H SGQ for one (1) hour.

for ten 10 hours in an au dred and twenty parts of tartaric acid, and four hundred iron. Print this paste onto the material dry and then pass the materiaflfor aboutfift'een (15) seconds through a fourteen (14)-per cent. solution of caustic soda at a temperature of about-seventy (70) degrees centigrade,wash, and then pass the material through sulfuric acid (containing about thirty-five per Wash well, soap, 2' T treat lightly with chlorin.

.1 recess using steamy-Prepare a paste containing two hundred (200) parts of a ten (10) per cent. paste of the new coloring-matter, eighty (80) parts of stannous oxid, (containing fifty per cent. of the pure compound,) fifty 50) parts of glycerin,and six hundred and seventy (670) parts of thickening T.

. This thickening T is prepared from three hun- (320) parts of asixty per cent. dextrin thickening, three hundred and forty (340) parts ofa fifty (50) per cent. gum thickening, and fourteen hundred and fifty (1,450) parts of a forty-one (41) per cent. caustic-soda solution. Print the paste onto the material and then dry at a temperature of from forty (40) to fortyfive (45) degrees centigrade, steam for five. (5) minutes in a Mather Platt apparatus, wash, treat lightly with chlorin, and then soap.

Now what I claim is 1. The process for the production of coloring-matter of the anthracene series by heating a hereinbefore-defined beta-methyl-anthraquinon body with a condensing agent.

2. The process for the production of color ing-matter of the anthracene series by heating betamethyl-anthraquinon witha condensing agent.

3. The process for the production of color ing-1natter of the anthracene series by heating beta-methyl-anthraquinon with alcoholic caustic potasl 4. As a new article of manufacture the coloring-matter of the anthracene series which can be obtained by heatingahereinbefore-defined beta-methyl-anthraquinon body with a condensing agent,'whic coloring-matter crystallizes from nitrobenzene in golden-yel- .low crystals which are tiifficultly soluble in whereof I have hereunto set presence of two subscribing MAX HENRY ISLER.

Witnesses:

J. ALEX. LLOYD, Jos. H. LEUTE. v

IIO 

